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Review
. 2018 May;38(3):775-828.
doi: 10.1002/med.21466. Epub 2017 Sep 13.

Biologically active quinoline and quinazoline alkaloids part I

Affiliations
Review

Biologically active quinoline and quinazoline alkaloids part I

Xiao-Fei Shang et al. Med Res Rev. 2018 May.

Abstract

Quinoline and quinazoline alkaloids, two important classes of N-based heterocyclic compounds, have attracted tremendous attention from researchers worldwide since the 19th century. Over the past 200 years, many compounds from these two classes were isolated from natural sources, and most of them and their modified analogs possess significant bioactivities. Quinine and camptothecin are two of the most famous and important quinoline alkaloids, and their discoveries opened new areas in antimalarial and anticancer drug development, respectively. In this review, we survey the literature on bioactive alkaloids from these two classes and highlight research achievements prior to the year 2008 (Part I). Over 200 molecules with a broad range of bioactivities, including antitumor, antimalarial, antibacterial and antifungal, antiparasitic and insecticidal, antiviral, antiplatelet, anti-inflammatory, herbicidal, antioxidant and other activities, were reviewed. This survey should provide new clues or possibilities for the discovery of new and better drugs from the original naturally occurring quinoline and quinazoline alkaloids.

Keywords: bioactivities; camptothecin; quinazoline alkaloids; quinine; quinoline alkaloids.

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Figures

FIGURE 1:
FIGURE 1:
Chemical structures of historically important quinoline and quinazoline alkaloids 1–4
FIGURE 2:
FIGURE 2:
The chemical structures of camptothecin analogs 5–14
FIGURE 3:
FIGURE 3:
The chemical structures of camptothecin analogs 15–18
FIGURE 4:
FIGURE 4:
The chemical structures of camptothecin analogs 19–22
FIGURE 5:
FIGURE 5:
The chemical structures of camptothecin analogs 23–27
FIGURE 6:
FIGURE 6:
Chemical structures of compounds 28–51
FIGURE 7:
FIGURE 7:
Chemical structures of compounds 52–63
FIGURE 8:
FIGURE 8:
Chemical structures of compounds 64–70
FIGURE 9 :
FIGURE 9 :
Chemical structures of compounds 71–82
FIGURE 10:
FIGURE 10:
Chemical structures of compounds 83–89
FIGURE 11:
FIGURE 11:
Chemical structures of compounds 90–97
FIGURE 12:
FIGURE 12:
Chemical structures of compounds 98–110
FIGURE 13:
FIGURE 13:
Chemical structures of compounds 111–118
FIGURE 14:
FIGURE 14:
Chemical structures of compounds 119–131
FIGURE 15:
FIGURE 15:
Chemical structures of compounds 132–137
FIGURE 16:
FIGURE 16:
Chemical structures of compounds 138–161
FIGURE 17:
FIGURE 17:
Chemical structures of compounds 162–176
FIGURE 18:
FIGURE 18:
Chemical structures of compounds 177–189
FIGURE 19:
FIGURE 19:
Chemical structures of compounds 190–195
FIGURE 20:
FIGURE 20:
Chemical structures of compounds 196–205
FIGURE 21:
FIGURE 21:
Chemical structures of compounds 206–216
FIGURE 22:
FIGURE 22:
Chemical structures of compounds 217–220
FIGURE 23:
FIGURE 23:
Chemical structures of compounds 221–228
FIGURE 24:
FIGURE 24:
Chemical structures of compounds 229–235
FIGURE 25:
FIGURE 25:
Chemical structures of compounds 236–247

References

    1. Prajapati SM, Patel KD, Vekariya RH, Panchal SN, Patel HD. Recent advances in the synthesis of quinolines: a review. RSC Adv. 2014;4:24463–24476.
    1. Wiesner J, Ortmann R, Jomaa H, Schlitzer M. New antimalarial drugs. Angew Chem Int Ed. 2003;42:5274–5293. - PubMed
    1. Manske RH. The chemistry of quinolines. Chem Rev. 1942;30:113–144.
    1. Tumer RR, Woodward RR. The chemistry of the Cinchona alkaloids. In: Manske RHF, ed. The Alkaloids. New York: Academic Press; 1953:16.
    1. Wall ME, Wani MC, Cook CE, Palmer KH, McPhail AT, Sim GA. Plant antitumor agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminate. J Am Chem Soc. 1966;88:3888–3890.

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